Quaternary ammonium diorganoboron compounds



United States Patent US. Cl. 260-462 2 Claims ABSTRACT OF THE DISCLOSURE The present invention relates to new chemical compounds having the following formulas:

t it [his] I wherein the R groups are any combination of C -C hydrocarbyl groups; and Z is an ortho disubstituted benzene ring, or a 1, 2 or 2, 3 disubstituted naphthalene ring.

CROSS-REFERENCE TO RELATED APPLICATION This application is a division of S.N. 525,624, filed Feb. 7, 1966, now US. Pat. 3,403,304.

BACKGROUND OF THE INVENTION The present invention relates to new chemical compounds.

The quaternary ammonium compounds of the present invention have utility as the electrolyte solute of electrical capacitor electrolytes. They are crystalline compounds of high purity and have excellent solubility characteristics in a variety of solvents.

DETAILED DESCRIPTION OF THE INVENTION The following examples in which parts and percentages are by weight unless otherwise stated, illustrate the more detailed practice of the invention but are not to be construed as limitative. The salts prepared in these examples were analyzed for nitrogen by the Kjeldahl method and for carbon and hydrogen by standard combustion techniques.

Example I.-Tetramethylammonium borodisalicylate 3,539,614 Patented Nov. 10, 1970 "ice The following structure has been proved for this compound:

H H o 0 Following the same general procedure tetraethylammoni-um borodisalicylate and benzyltrimethylammonium borodisalicylate were formed.

Example II.Benzyltrimethylammonium borodi (2- hydroxy-l-naphthoate) To a hot, filtered solution of 2-hydroxy-1-naphthoic acid (0.1 mole) in ethanol were added successively a solution of boric acid (0.05 mole) in hot water and benzyltrimethylammonium hydroxide (42 gms. of a 40% solution in methanol). Some methanol was added and the mixture was heated to solution.

On cooling, addition of ether, and scratching, the product 12 gms. (45%) of an off white solid was obtained. After crystallization from a 2-propanol-water mixture and washing with acetone, the product had a melting point of -187 C.

Analysis.Calculated for C H BNO theoretical (percent): N, 2.63. Found (percent): N, 2.58.

The following structure has been proved for this compound:

O O 0 Ha (i-O 0 s CH3 0 O Following the same general procedure the following compounds were formed: tetraethylammoni-um borodi (3 hydroxy-2 napthoate) tetraethylammonium borodi (l-hy droxy-2-naphthoate); and tetraethylammonium borodi (2- hydroxy-l-naphthoate) Example IlI.Tetramethylarnmonium borodicatecholate A mixture of catechol (0.15 mole), boric acid (0.25 mole) and tetramethylammonium hydroxide (0.25 mole as a 10% aqueous solution) was heated to solution. Water was removed by a water pump. The product Was crystallized from an isopropyl alcohol-methanol mixture; yield was 71.7%. Recrystallized from an isopropyl alcoholmethanol-ethyl ether mixture, the melting point was 288- 290 C.

Analysis-Calculated for C H BNO M.W.301.l5;' theoretical (percent): C, 63.81; H, 6.69; B, 3.59; N, 4.65. Found (percent): N, 4.34.

The following structure has been proved for this compound:

W HaCN-CHa B CH3 0 o In a like manner the tetrahydrocarbyl-ammonium salt of the bisdiolborate of 1,2 or 2,3 dihydroxy naphthalene may be formed. These compounds have the following structure:

@QXIQQ Example IV An electrolyte was prepared by dissolving 4% of tetramethylammonium borodicatecholate in dimethylformamide. Two groups of commercial aluminum foil 5 and 75 volt capacitance sections were impregnated with this electrolyte. The following table gives life test data obtained at 125 C. The values given are averages of 5 units of each rating.

and

5 volt 75 volt Capaci- Capacitance Rx C I( a) tance RxC Iota) Hours:

The foregoing data indicate the capacitors are electrically stable and improve somewhat with time from a leakage current standpoint.

Example V An electrolyte was prepared by dissolving 8% of benzyltrimethylammonium borodisalicylate in dimethylformamide. A group of commercial aluminum foil 50 volt units was impregnated with this electrolyte. The following life test data was obtained at 85 C. The values given are the averages for 5 units.

50 Volt Capacitance RxC I(l-ta) As in the previous example, the results indicate electrical stability with a good improvement in leakage current over the duration of the test period.

The electrolyte systems contemplated herein are not limited to those wherein the solvent is dimethylformamide since other solvents and mixtures of solvents may be employed. For example, water, formamide, the glycols, etc. and mixtures thereof may be employed. It is also to be understood that the electrolytes of the present invention have utility in capacitors other than aluminum, e.g. tantalum, etc.

Since it is obvious that many changes and modifications can be made in the above-described details without departing from the nature and spirit of the invention it is to be understood that the invention is not limited to said details except as set forth in the appended claims.

What is claimed is:

1. A compound having a formula selected from the group consisting of and References Cited UNITED STATES PATENTS 1,975,890 10/1934 Williams et al. 260462 2,497,521 2/ 1950 Trautman 260462 2,568,472 9/ 1951 Traut man 260462 3,005,012 10 /1961 Mulloy 260462 3,169,983 2/1965 Hunter 260462 3,373,170 3/1968 Jones 260462 LEON ZITVER, Primary Examiner J. E. EVANS, Assistant Examiner 

